


Creepypasta Yaoi

by Risingdawn66



Category: Creepypasta - Fandom
Genre: Fluff, M/M, Self-Insert, Smut, Yaoi
Language: English
Status: In-Progress
Published: 2018-10-23
Updated: 2018-11-06
Packaged: 2019-08-06 13:25:30
Rating: Mature
Warnings: No Archive Warnings Apply
Chapters: 15
Words: 15,574
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/16388546
Author URL: https://archiveofourown.org/users/Risingdawn66/pseuds/Risingdawn66
Summary: These are my Creepypasta Yaoi stories I'm excluding a few I don't like.





	1. JeffxBen

**Summary for the Chapter:**

> Jeff got Ben to fall asleep and he was going to as well, but instead he got a bit needy and explores Ben's sleeping body.

It was a late night and as usual ben was up on the top bunk playing videogames on silent while jeff was sleeping on his bed and he used headphones. Jeff grumbled and rolled onto his side from the light of the DS and sat up pulling his sleeping mask off. "Ben go to sleep already its, its fucking 11:30 at night dude!" He yelled at ben startling him as he dropped his DS on the floor making the game glitch up and freeze as he jumped down picking it up "no no no no no NO! My game i was in the middle of a pokemon battle with the elite four no now its all lost!" He whined as jeff rolled his eyes smacking the back of his head "just fucking redo it then" he grumbled as ben looked back at him "but it took me forever to get there and i had to beat the elite four before i could save it again now im gonna have to start all the way back at the eighth gym" he whined sitting on his butt and started crying and jeff sighed sitting beside him "ben you'll be fine" he said softly as ben hugged him puffing his cheeks a little "your a meanie you know" jeff chuckled softly stroking bens hair hugging him back "hey what else am i supposed to be?" He chuckled softly as ben nuzzled up to him happily.

After a few minutes of nuzzling jeff ben yawned softly laying his head on jeffs chest happily as jeff smiled and picked him up walking over to the bed he laid down and set the sleeping elf boy next to him pulling him close as he fell asleep too.

Bens POV

I grumbled tossing my head opening my eyes to jeff sucking on my neck and pinching my nipples. "Je-Jeff!" I squeal blushing deeply and trying to push him off as i heard a soft grunt and a low growl i stopped as he held my shoulders pinned to the bed staring into my eyes his eyes were hazy with lust "stop moving ben" he grumbled and kneed my crotch my eyes go wide as i gasp blushing even more as he smirks grinding his knee to the bulge in my pants as i bite my lower lip and he pulls my tunic off the rest of the way leaving me in my pants and boxers as i breath heavily. "Je-jeffy stop" i whine softly as jeff teases and sucks my nipple making me moan loudly. He chuckled deeply and pinched my stomach and hips as i softly whine and rub against his knee moaning softly "i see your starting to enjoy it ben" he said huskily and left a trail of kisses down my stomach.

Jeffs POV

I chuckle deeply kissing ben as i trailed down to his pants and i suck and nip at the bulge as ben moaned louder. I love it when ben moans his body is so honest with emotions and hes just so adorable i cant help myself. I pull down his pants and boxers and give his shaft a slow long and teasing lick from the base to the tip as ben pants and moans even louder and i chuckle taking his full length into my mouth "je-jeff oh my haa" he groans softly bucking his hips a little and i bob my head sucking and licking the tip in the process.

I start to taste something in the back of my throat knowing ben was going to cum soon i pulled away as he whined and i smirk "dont worry benny I'll make you feel really good" i chuckle more and flip him over raising his bum as he pouts a bit and i chuckle taking my own member out and i position myself.

Third Person POV

Ben whined as he was flipped over facing the bed and puffed his cheek as jeff chuckled and he shivered a little when jeff positioned himself at his unprepared entrance and bit the pillow as jeff started slowly pushing in groaning loudly "god damn ben your so fucking tight" he groaned louder pushing in the rest of the way as ben trembles lightly from the pain and jeff waits for him to adjust to his size and placed soft kisses on his back as he carefully thrusted into him receiving a very loud moan of pleasure and he nodded softly going faster. Ben moaned and panted heavily biting at his pillow "je-jeff im gonna cum" he whined as jeff kept thrusting into him "i am too ben" he groaned softly. After a few more thrusts ben moaned loudly in pleasure as he came all over the sheet as jeff thrusted deeply cumming in him filling his ass and pulled out panting heavily collapsing beside ben pulling him close.

After a few minutes of them gasping and taking deep breaths trying to steady their breathing ben faced jeff and nuzzled close "jeff that was amazing" ben said between breathes and smiled as jeff hugged him "yeah it was ben" he said pulling a blanket over them and smiled falling asleep.


	2. MaskyxHoodie

**Summary for the Chapter:**

> Hoodie hasn't become a proxy yet and Masky was sent to check on him.

(Masky is Slendys proxy but Hoodie is not yet also this is Hoodies POV)

I was just sitting on the couch at home watching TV as it's late, and my parents are out. I always stayed up till they were home, because I never liked to go to sleep when I'm the only one home.

It was quiet other than the noise from the TV as I jumped hearing the grandfather clock go off.

"It's midnight they're never this late… I'll call them" I say to myself quietly as I grab the house phone and call mom.

"Mom are you there where are you?" I say into the phone getting chills down my spine with the response.

"They aren't coming home they're dead Brian" a male voice says as my eyes widen.

"Ho-how do you know my name, Who are you?!" I say frightened as I hear laughing on the other end.

"Just call me Masky kid I'll be coming to get you soon" he says then hung up as I throw the phone scared and I get up locking all the doors and windows as I sat on the couch again. I was trembling as I was getting tired as my eyelids were growing heavy.

'No got to stay awake' I think to myself as I kept my hand gun on the stand next to the couch. I close my eyes as my head leans down, but I snap my eyes back open and lift my head up looking at the window to see it's open.

"Damn it I close my eyes for thirty seconds and something happens" I say softly as I frown hearing a voice.

"Pfft thirty seconds more like thirty minutes Brian" it was a deepish voice as my arm snaps over and I grab my gun pointing and shooting at the masked man hitting the wall beside his head since he moved at the last minute.

"Wow you really are a good shooter would've shot my head if I didn't move, and you barely took five seconds to aim too" he says smirking and walking towards me as I pull the tab at the back as the barrel rotates a new bullet in place as I aim at his head "don't come any closer" I say my voice a bit deeper as I'm scared, but putting up a brave front.

"Oh wow your being brave now aren't you Brian" he says stopping and putting his hands up as I stand.

"Be quiet your the one from the phone call so your name is Masky" I say walking towards him as he kept his hands up smiling under the mask as he thought it was adorable at how I was trying to be brave. I walk closer to him as I was shorter than him as I pout and pull my orange hood up it covering most of my face as it hides the light blush. Masky smirks under his mask as I kept my gun in my hand and finger on the trigger as I soon reach my hand up and I grab the base of his mask as he raises his eyebrows.

"Hey what d'you think your doing?" He asks gently grabbing my wrist as he lifted my hood to see my blush.

"Hehe cute" he says as I blush more.

"Shu-shut up" I say embarrassed as he chuckles softly as he lets my wrist go. I soon lift his mask up as I blush more looking at him and he smiles sweetly.

"Hehe your so cute Brian happy to see my face?" He asks as I have a small bulge in my pants that he gently pokes.

"Ah don't perv" I say embarrassed as I pull away a little making him chuckle when I returned to the closeness we were at before. I soon put my guns safety on and put it in my back pocket as I study his face the bright blush still present on my cheeks being hidden under my hood. Maskys eyes widen from shock as I go on my tiptoes and kiss him deeply and I pull away pulling my hood all the way over my face being embarrassed as he chuckles more.

"Aww so innocent, cute, and easily embarrassed" he says smiling big as I hug him and bury my face in his chest as I start to grind against his leg and he smiles hugging me back and laughs softly hearing a moan escape my lips.

"Hold on let me sit down" he says pulling me to the couch as he sat and removed the gun from my pocket setting it on the side table and patted his leg. I pant as I plop down onto his leg as I moan out in pleasure my eyes closed, and he smiles as he took his mask off the rest of the way. He pulled my hood down placing his mask on my head sideways and takes his phone out taking a picture. I was blushing deeply with quite the lustful expression as he smiles and leans back letting me enjoy myself now.

I moan out as I grind against his leg and move down to his knee as I moan louder when I grind against it.

"Wow you really are a virgin becoming such a moaning mess just from grinding against my leg" he says smiling and gently patting my head as I pant and nod "it feels so good" I say softly as he smiles and takes my pants and boxers off as I blush and he takes his own pants and boxers off.

"Ah wa-wait Masky I don't want to do this this fast" I say starting to panic as he smiles and gently sets me onto his leg once more.

"No no I'm letting you go at your own pace I just thought it would feel even better if you rubbed your member fully against my leg" he says as I nod. I soon blush more as I buck my hips back and forth on his leg as I lean my head back and moan out more.

"Ahh it does feel way better" I say softly as he nods and pulls me closer to him as he hugs me and holds me close and I blush and rub my member against his nervously as I moan out but look at the other as he groaned. I soon get the idea as I rub and grind our members together and I soon moan loudly as I hug him tightly and bury my face in his chest as I cum hard as he rubs my back smiling since I fell asleep after cumming.

"Aww he fell asleep that's so cute. Goodnight Hoodie" he says softly as he kisses my head and pulls a blanket over both of us and fell asleep.


	3. ZalgoxSlenderman

**Summary for the Chapter:**

> Slenderman was roaming through his woods when he got a sudden unwanted visitor

:Slendy's POV:

I was minding my own business as I walked through my forest. I kept watch, because I was looking for foolish people that wandered into my forest. I smirk to myself as I see a teenage girl looking around completely lost the perfect target is what I saw her as. I was so focused on killing the girl that I fail to notice a lingering presence getting closer to me. I grab the girl as my tendrils go through her back killing her, and I smile satisfied by her corpse now lying on the ground lifeless. I was about to leave, but I flinch and growl feeling someone touch my arm as I turn around quickly not seeing anyone.

"That's weird I could've sworn someone just touched my arm" I say softly as I growl and look around not seeing anyone, but I yelp in surprise as I was pinned to a tree by this person.

"Unhand me right now!" I yell pissed off as I hear a deep spine tingling laughter as my nonexistent eyes opened wide 'no not him' I think to myself as Zalgo smirks and leans over my back.

"Hey Slender it's nice to see you" he says with a smirk as I struggle becoming scared as he laughs more.

"You're not getting away from me Slendy" he says gripping my wrists tighter as I flinch. He smirks and takes my wrists with just one hand holding them above my head as he leans his chest onto my back and runs his hand up under my shirt as my eyes widen.

"Stop right now!" I yell my tendrils shooting out as he smirks more and licks one as it flinches away and my body shivers.

"Hehe you're so cute Slendy" he says chuckling as he nips one of my tendrils as I jolt a light blush spreading across my cheeks.

"Ah no stop it" I say embarrassed as my mouth opens showing sharp teeth as I start to breathe hard and pant. He smirks and nips on my tendril more as I blush deeply and moan softly.

"Hehe so naughty Slendy" he says as he pinches one of my nipples making me jolt and moan once more as he released my hands as I pant and scratch the tree moaning more.

"Ah ah Zalgo" I say panting and blushing as he laughs.

"Hehe wow Slendy so lude" he says using his free hand to unzip my jeans as he kept pinching my nipple and licking my tendril that's near his mouth as I moan more. He soon pulled my pants and boxers down to my knees as I blush deeply and pant.

"Not fighting it anymore Slendy?" He asks with a smug smirk as I nod a little.

"Good" he says rubbing my butt and soon shoving a finger in me as I moan loudly my nails digging deeply into the tree bark as he smirks pushing it in the rest of the way as he moves his other hand grabbing my member.

"Ah Zalgo mo-more please" I moan out as he smirks and strokes my member and thrusts his finger in me adding a second one forcefully as I groan loudly at the slight pain. He smirks more as he thrusts his fingers roughly and strokes me fast as I pant and was reaching my limit very quickly as he stops pulling his fingers out of me as I whimper wanting him to continue.

"No please don't stop" I whine out softly as he chuckles as I was already leaking precum my tip as he pulls his other hand away taking his member into his hand and positioning at my entrance making me blush.

"Aw but don't you want this in you?" He asks clearly enjoying this as I whimper remembering how big he is and I wasn't fully stretched but I really want it so I sigh and nod.

"Yes I want it so badly I want you deep inside" I say blushing deeply as I felt embarrassed and ashamed as I said this. He smirks and thrusts in fully without warning as I scream out in pain, and he laughs enjoying my screams as he rocked his hips back and forth to get me adjusted as I pant. He kept doing this as I pant and soon moan gently as he was rubbing against my prostate as I blush wanting him to move so I carefully wiggled my hips as he chuckles deeply.

"Oh you want me to move?" He asks as I nod and he chuckles and nods.

"Ok I will" he says before pulling out almost all the way and slamming back in as I moan loudly and he starts thrusting in me at a very fast and rough pace. I moan and mewl gripping and scratching the tree as he held my hip with one hand and stroked my member with the other as I kept moaning more.

"Ah Zalgo ahhh it feels so good haa I can't hold it much longer" I say out as he soon went faster groaning as I gasp and moan out with each violent thrust. He soon slammed into my prostate as I scream in pleasure and cum as he grunts and cums filling me. I pant and shake as he pulls out smirking when I slid onto the ground panting hard and slightly shaking from the pleasure as I couldn't think straight feeling his warm cum drip from me.

"Hehe see you later Slendy" he says before leaving me and disappearing like he always did he wouldnt even help me get home. I sigh and stand getting my clothes fixed as I stumbles home and sat on the couch soon falling asleep.


	4. RandyxJeff

**Summary for the Chapter:**

> This occurred before the accident and Randy's just a big jerk to poor Jeff.

:Before accident:

:Jeff's POV:

It was the usual day at school being picked on and bullied by Randy. I sigh to myself as I sit alone at the lunch table, because my brother Liu is home sick. I eat quietly as Randy approached me and I frown.

"What do you want Randy?" I ask annoyed as he smirks.

"Oh why are you sitting alone Jeffy got no friends?" He says snickering as I roll my eyes. He smirks at me and grabs my arm as I growl and struggle to get free.

"Hey let me go!" I yell as he yanks me from the table and drags me from the cafeteria as I struggle.

"Stay still Jeffery!" He says aggressively as he drags me into the bathroom and pins me against the wall in one of the stalls smirking big. I frown and struggle more as he grips my wrists above my head and laughs.

"You're so weak Jeff" he says gripping my chin as I bite his hand and he growls slapping me.

"Don't do that again Jeffery!" He shouts and slams me against the wall as I gasp my breath knocked from me as he smirks and laughs. He soon used his one free hand and undid my belt as I growl and he takes it off me tying my hands together. He unzips my jeans as I frown and start struggling violently.

"What the fuck do you think your doing!" I yell as he slaps me across the face to tell me to be quiet as i frown. He continues to unzip my jeans, and then he pulled them down to my knees as I blush a bit.

'What is he doing he's never gone this far' I think to myself as he grips my crotch making me gasp in surprise. He smirks as he palms my crotch making me blush deeper and make small sounds as I turn my head away.

"Aw are you enjoying yourself Jeffery?" He asks smirking as I growl but mewl right after as he gave my small bulge a squeeze.

"Ah what the fuck stop it" I say my voice shaky and my face bright red. He smirks as he kept rubbing my bulge and soon pulled my boxers down watching my half hard member spring up.

"Oh I see someone's liking their treatment" he says as I blush more and pant softly as I try to hide my face as he chuckles. I pant and let out a shaky moan as he wraps his hand around my balls and gives them a gentle squeeze.

"Ah no stop it" I whimper out as he laughs softly and takes my member into his mouth making me moan as it felt good. He took my whole length in easily as he bobs his head sucking hard and I moan loudly as he smirks.

"Ah Randy no sto-stop it" I whimper out clenching my hands and slightly wiggling around as I mewl cutely. Randy soon pulls off and smirks as he strokes me making me moan more as I pant.

"Aw Jeffery you're so cute" he says chuckling as he stood and pushed me onto my knees as I pant. He smirks big as he unzips his own pants and takes out his big hard member as I blush deeply.

"Suck it" he says sternly as I nod and put the tip in my mouth sucking as I start to bob my head taking as much as I could in. He groans in pleasure burying his hands into my hair as he grips my head and thrusts into my mouth making me gag slightly.

"Ah Jeff your mouth feels so fucking good" he groans out as he kept bucking his hips making me whimper and suck more. He soon pulls me off as I pant. My face is deep red as he smirks and yanks me up pinning me to the wall again, but this time I'm facing it. My body trembles as I don't know what he's doing and he laughs shoving a finger into me as I moan loudly from the sudden intrusion.

"Ah Randy" I moan out blushing even more as he laughs and pumps the finger in me as I moan more since it felt good. He kept this up and soon shoved a second finger in me as I moan out and he pumps them faster as I pant and moan my face squished against the wall. He soon pulls his fingers out and leans over me positioning himself as I squeak feeling his tip at my entrance.

"You're gonna feel really good after this" he whispers in my ear making me shudder as he thrusts in fully making me scream in pleasure as he held my hips grunting.

"Damn Jeff you're really tight" he says grunting as he started thrusting making me moan with each thrust. I didn't understand why he was doing this to me all of a sudden, but my mind wasn't working properly enough to care as I mewl and whine in pleasure. Randy thrusted roughly as he grunts and gripped my hips hard making me moan loudly as my mind didn't know right from wrong anymore.

"Ah yes Randy ah more I want more" I say out as he laughs and grips my member stroking me as he thrusts faster making me moan louder as he grunts and slams into me as I scream his name cumming all over the wall as he grunts and cums hard in me. I pant as he smirks and pulls out undoing the belt around my wrists as I pant sliding to the floor as Randy smirks satisfied with his work as he left me there. I soon have tears rolling down my cheeks as I got up and cleaned everything up and went to the office to call mom and dad to bring me home. I went home not giving Randy a look or thought as I walked out of the building. Once I got home I went straight to Liu and tell him what happened tears rolling down my cheeks as he held me and comforted me as I soon fell asleep.


	5. LjxJeff

**Summary for the Chapter:**

> This is before the accident and Lj just wants to comfort Jeff, but gets a bit carried away.

:Before accident:

:Jeff's POV:

I was in my room crying loudly from yet another day of being bullied and pushed around by Randy. I sniffle and wipe my eyes not like it would do much to stop the tears from falling. I sat at the back of my bed when I hear a soft voice.

"Hey kid you ok?" The voice asks as I look around trying to find where the owner of the voice is.

"Who are you? How did you get in my room!" I shout as I kept crying a shadowy figure approaching my bed.

"Calm down I'm right here kid and you left your door open so I followed you in" he says stopping at my bed as I look at him.

"Who are you?" I ask again as he smiles big and bows.

"The name is Laughing Jack and I'm your new best friend" he says smiling at me as I scoot into the corner on my bed.

"Your not human how can I trust you" I say being suspicious.

"Yeah I'm a lost imaginary friend. I won't hurt you though" he says soon sitting beside me as I try to scoot away.

"Yeah no I'm all good don't need any imaginary friend I'm not 3" I say as he pouts.

"Aw come on that's not nice" he says hugging me as I push him off frowning.

"I said no" I say getting annoyed as he frowns.

"Hey kid I've got candy" he says as I perk up hearing him say candy. He chuckles and pulls a small bag out of his pocket and takes a lollipop giving it to me as I take it.

"Thanks" I say quietly as he nods giving me a big smile. I ate a few of the lollipops he gave me as he held another one out to me.

"No thanks I'm good now" I say smiling as he frowns.

"Awe come on one more" he says trying to coax me into taking it as my smile starts fading.

"I said no Lj I've had enough candy" I say as he frowns and growls grabbing my chin and forcing the lollipop in my mouth catching me by surprise.

"Nobody says NO to me kid!" He says aggressively shoving the lollipop further in my mouth before his eyes widen and he pulls away frowning like a puppy that's been scolded.

"I-I'm sorry" he says softly as I take the lollipop out of my mouth and cough softly.

"What the hell dude!" I say pissed as he whimpers.

"I'm sorry I don't know what came over me" he says as I sigh and put the lollipop back in my mouth to make him happy as he smiles again. I sat there sucking on the lollipop as he watches me and gently grabs it and moves it in and out of my mouth as I blush and suck more. My body was starting to heat up as I look at the guy and he's blushing lightly as he moved the lollipop in my mouth. I make soft sounds as I sucked closing my eyes and he smiles pulling me close holding me to his chest as I blush.

"You're really cute kid" he says softly as I blush more. He soon took the lollipop from my mouth and kisses me deeply as I shyly kiss back. He pulls the back side of my pants down along woth my boxers as I was too occupied with the kiss to notice. I squeak as I felt the sticky lollipop poke at my entrance as I blush deeply looking at Lj.

"Ah wha-what are you doing?" I say embarrassed as he smirks a bit and pushes the lollipop into me making me squeak again.

"Ah what the heck ah no take it out it's not supposed to be there" I say panicking as he hushs me and held my head to his chest as he moved the lollipop in me as I gasp.

"Ah no stop please stop it feels weird" I say wiggling around as he thrusts it harder making me moan softly my face bright red. He smirks and kept thrusting the lollipop in me as I whimper and wiggle around panting. He pulls my pants and boxers down to my ankles and moves me onto my stomach my butt propped in the air as I pant and moan from him moving the lollipop more. He soon takes the lollipop out and shoves two of his fingers into me making me squeak loudly like a small mouse. He chuckles deeply as he moves his fingers deeper in me.

"You like this don't you kid" he says deeply as he leans over me and soon stroked my hard member making me moan more. He soon pulls his fingers out making me whine and he laughs poking his own hard member at my entrance as I squeak again.

"You want this don't you? You want my huge lollipop buried deep inside you" he whispers in my ear as I nod panting.

"Ah yes I want it I want your huge lollipop deep inside me I wanna be filled with it" I moan out as he smirks and slams into me as I moan loudly and he grunts.

"Ah damn kid your really tight" he says grunting as he started to thrust. I moan loudly wiggling around as I pant and thrust back on him wanting more.

"Ah more go faster I want more please go faster" I whine out as he nods and thrusts faster as I pant and he strokes me faster.

"Ah Lj I'm close" I whine out as he thrusts faster and I moan loudly cumming all over the bed as Lj grunts and cums deep in me as he fills me with cum. I pant and collapse on the bed as he pulls out and snuggles my back happily and I smile.

"Thanks Lj that made me feel better" I say panting as I nuzzle Lj and he happily nuzzles me back as I yawn.

"Aw you're sleepy now" he says smiling as I pant and cuddle closer soon falling asleep as he holds me close.


	6. ZalgoxSlenderman 2

**Summary for the Chapter:**

> Slenderman got back to the mansion and into his office to work, but Zalgo had other plans for him.

:Slendy POV:

I sigh a bit when I lay on the couch grunting a bit from the long walk home. I slept quietly for a while not bothering myself with cleaning out first just wanting to sleep. I soon woke though to see Masky and Hoodie hovering over the couch staring at me as I sigh a bit. I slowly sat up wincing and flinching in pain as Masky gently pulled me back against the couch as if knowing what happened.

"Sir please relax alright me and Hoodie will take care of you" he says calmly as I nod quietly putting my head down feeling ashamed before teleporting to my room in shame. Masky sighs while Hoodie quietly got something along with a blanket walking upstairs to my room. I laid quietly soon feeling something warm leaking from myself as I panicked a bit feeling the back of my pants and raising my hand seeing it had a lot of fresh blood on it. I frown shaking a bit knowing Zalgo did some real bad damage to my body this time. I quickly turned my head to the door sighing softly when I see Hoodie walk in.

"Let's get you a shower first before you relax sir" He says as I nod quietly. Hoodie helped me up and to my personal bathroom as I winced.

"Careful sir" He says as I nod. Hoodie started the shower making sure I would be okay before leaving as I got in relaxing under the water. Once I was done and got out I got dried and dressed walking from the bathroom my head down when I notice Hoodie put a towel on the bed. I sigh to myself as I laid down and slept for a long while. After a few hours I bolted awake feeling a weight getting on my bed as I stare up at Zalgo who was smirking. I start to shake in fear as he chuckles deeply.

"Miss me Slenderman?" He asks smirking big as I tremble. Masky and Hoodie came to check on me trying to open the door but Zalgo had locked it. He stares down at me smirking big when he heard my proxies voices.

"Sir why is the door locked you alright?" Masky asks as I have Zalgo staring down at me with a big smirk. I was quiet for a minute or two deciding to not put my proxies in any danger.

"Yes Masky and Hoodie I'm just fine you both can go back downstairs" I say keeping my voice calm as they walked off downstairs.

"Good choice Slendy~" He says chuckling darkly and snapped his fingers making my room soundproof.

"Now no one but me shall hear your screams" He says smirking as I gulp trembling in fear my body still hurting and not fully recovered from last time. I winced when Zalgo basically ripped my pants and boxers off as I turn my head away. Zalgo chuckles darkly as he ran his hands over my thighs.

"Mmm~ You'll make all those sounds for me like you did last time right?" He asks smirking as I blush deeply and whimper when he shoved two fingers in me stretching me slightly. I whimper more as he chuckles and pulls his fingers out lifting my legs up and over his shoulders.

"Please don't Zalgo" I say frowning as he chuckles darkly taking his member and slammed into me as I yelp in pain. Zalgo grunts a bit sensing my pain as I whimper. Zalgo sighs as he stayed still for a while deciding to be nice and let my body adjusts to not hurt me worse. I pant after about five minutes and gently rock my hips letting out a gentle moan blushing. Zalgo smiles and pulls out thrusting back in as I moan blushing more.

"This better for you Slendy?" He asks softly as I nod. He nods back and thrusted at a gentle pace groaning as he wrapped his arms around my thighs while thrusting. I moan and gently grip the sheets panting as Zalgo was being gentle.

"Ahh Zalgo this feels much better than before" I say panting and moaning as I wrap my arms around his neck while he leaned down. I pant and open my mouth kissing Zalgo passionately as he kisses back and continued to thrust grunting. I moan softly as I nuzzle him and he kept going a bit faster as I moan more.

"Ahh Zalgo I'm gonna cum!" I moan out as he nods and thrusted more hitting my prostate as my back arches as I moan loudly Zalgo snapping his finger when I moan. I didn't notice as I moan cumming and he cums in me as I pant. I blush deeply hearing Masky and Hoodie run up the stairs. I pant looking at Zalgo embarrassed going very deep red when Masky and Hoodie came in seeing the situation of Zalgo being in me. I cover my face embarrassed as Zalgo chuckles softly slowly pulling out making me moan lightly. Masky and Hoodie blush deeply as they slowly close the door making Zalgo chuckle more.

"Zalgo! Why did you let them here me!" I whine loudly embarrassed as he chuckles. Zalgo laid down beside me pulling the blankets up as I blush being pulled close. I nuzzle him quietly as he smiles rubbing my back as I yawn.

"Get some sleep Slendy" He says sweetly as I nod and nestle close soon sleeping. Zalgo smiles holding me close and fell asleep being glad to make me feel good instead of awful. Me and Zalgo slept peacefully while downstairs Masky and Hoodie were quietly cuddling being dark red and embarrassed that they had asked in on us like that. They relax and sleep as the night went on.


	7. SullyxJeff

**Summary for the Chapter:**

> It was a foggy day when Jeff decided to visit his old now abandoned home being completely unaware that Sully was also there with some plans in mind.

Warning: Incest if you don't like please leave

It was a year after Jeff's accident as he is alone. On a foggy day Jeff decided to visit his old house the one he killed his family in. Jeff made it there and went in through the back as he looked around quietly unaware he was followed. Out of nowhere Jeff was pinned to the wall by someone older than him. Jeff growls deeply as he struggled in the others hold.

"The hell let me go!" Jeff yells struggling as the other wouldn't let go. Jeff managed to look at the person growling more when he realized it was his older brother Liu.

"Liu let me go!" Jeff yelled as Liu gripped Jeff's arms more keeping him against the wall while smirking.

"Liu's not here right now Jeff" Liu says chuckling darkly as Jeff growls more.

"Stop fucking around Liu!" Jeff says growling as he flinched when his arms were squeezed more.

"Liu's not here right now it's Sully" Liu says smirking as Sully was in control. Jeff was confused and growled more as Sully gripped Jeff's head growling back.

"That's enough Jeffery" Sully says growling as Jeff flinched when his head was squeezed. Jeff struggled till Sully hit Jeff's head against the wall being angered.

"I said enough!" Sully yells slamming Jeff's head to the wall again. Jeff whimpered when he started to feel blood running down the side of his face making Sully laugh loudly.

"What's the matter Jeffrey? Not so big and bad anymore now are you" Sully says laughing as Jeff whimpered.

"Now Jeff be a good boy and stay still as long as you do I won't hurt you anymore ~" Sully says smirking as Jeff nods whimpering. Sully let Jeff's hands and head go as Jeff stayed still.

"Good boy~" Sully says rubbing Jeff's hips making the other's eyes go wide.

"Su-Sully stop!" Jeff yells not expecting to be touched like that. Sully growls in return and slapped Jeff's ass hard making Jeff yelp.

"Don't talk back to me Jeffrey I shall do whatever I like!" He says loud and stern as Jeff flinched nodding quietly. Sully soon wrapped his arms around Jeff's waist and ran a hand on Jeff's crotch making him blush. Jeff shivered blushing as Sully smirks rubbing Jeff's crotch more making Jeff moan lightly.

"Ahh! Su-Sully ah no stop" Jeff whined blushing deeply and moaned while Sully continued to rub Jeff's crotch. Jeff moans panting leaning on the wall now gently gripping the wall. Sully smirks chuckling and gripped Jeff's crotch which made the smaller male's back arch a cute moan leaving Jeff's lips.

"Oh Sully!" Jeff moaned out bucking his hips while Sully gripped and rubbed Jeff's crotch more.

"That's it Jeffrey good boy" Sully says slipping his hand up Jeff's sweater and pinched his nipple. Jeff moaned drooling a bit panting heavily and kept bucking his hips wanting more.

"Ahh Sully mo-more more please!" Jeff whines making Sully chuckle and grind his hand to jeffs crotch.

"That's it Jeffrey beg for more~" Sully says chuckling soon grinding on Jeff's ass. Jeff moans out unbuttoning his own jeans panting heavily while Sully groaned grinding on Jeff's ass more.

"Sully please more I want you in me please" Jeff says pulling Sully's head down and kissed him feeling Sully's bulge. Sully was surprised from Jeff kissing him and in return kissed back passionately yanking at Jeff's boxers. Sully yanked Jeff's boxers down smirking and unbuttoned his own jeans grinding against Jeff.

"Good boy Jeffery very good boy very needy~" Sully says chuckling and took his hard member out rubbing against Jeff's entrance. Jeff blushes when Sully shoves two fingers in his mouth and sucked on them while Sully teased Jeff's nipple. Jeff mewls and moans while sucking on Sully's fingers panting when they were pulled from his mouth.

"Alright Jeffrey I'm gonna stretch you a bit alright" Sully says as Jeff nods moaning when one of Sully's fingers slipped into him. Jeff's back arched as he moaned out while Sully slipped a second finger in and started stretching. Sully chuckles when Jeff started rocking his hips moaning while being stretched a lot. Jeff pants drooling once Sully pulled his fingers out and got his hard member positioned at Jeff's entrance.

"Alright Jeffrey I'm going in" Sully says smirking as Jeff nods moaning loudly when Sully slammed in.

"Ahh Sully!" Jeff moaned blushing deeply and scratching at the wall panting. Sully chuckles gripping Jeff's hips as he started to thrust making Jeff moan loudly.

"Ahh Sully yes oh feels good more!" Jeff moans out as he pants Sully thrusting fast and hard groaning and holding Jeff close slamming in and out. Jeff threw his head back moaning loudly blushing deeply as he pants Sully kissing him. Sully grunts and groans thrusting harder as Jeff pants.

"Oh Sully I'm close I'm gonna cum!" Jeff moans out while Sully kept slamming in and out.

"Fuck me too Jeffrey!" Sully says grunting as he kept slamming Jeff moaning as his body shook and trembled. Sully grunts slamming hard as Jeff let out a very loud moan and came all over the wall while Sully grunts and came along in Jeff's ass.

"Mmm Jeff this feels good" He says as Jeff pants blushing deeply. Sully smirks pulling out as Jeff fell to his knees panting and leaning against the wall. Sully fixed his pants chuckling as he looked down at Jeff.

"Have fun cleaning up Jeffrey~" Sully says leaving Jeff to clean the mess. Jeff pants blushing deeply as he leaned on the wall frowning and watched Sully leave. Jeff whimpered when he was left alone and curled up crying as his body hurt. Jeff slowly stood up breathing a bit hard and pulled his pants up holding them up. He walked through the halls and went to the bathroom embarrassed now while he got a towel.

"Gotta clean myself up" Jeff says to himself tears rolling down his cheeks as he got his pants and boxers off slipping his sweater off. He walked to the mirror turning his head as he found the spot that was bleeding being glad it had stopped. Jeff wobbled to the tub falling to his knees breathing hard tears still rolling down his cheeks standing to turn the shower on. He got a wash cloth whimpering as he got in the shower sitting under the warm water crying in pain curling up.

"Stupid Sully stupid Liu" Jeff says crying and cleaned himself out whining. He soon started to wash up getting clean before getting out and dried off. Jeff got dressed before getting his knife from the living room and wobbled out of the house growling.

"Fucking hell it hurts so much" Jeff says crying as he leaned on a tree looking to Slenderman who appeared in front of him.

"Let's get you home Jeff" Slenderman says as Jeff nods taking Slendys outstretched hand being held close as they teleported to the mansion.

"Thanks Slendy" Jeff says as Slendy nods soon laying Jeff in his bed covering him up letting Jeff rest for a while. Jeff slept quietly while in the forest Sully chuckles being glad to have done that to Jeff.


	8. TrendermanxLost Silver

**Summary for the Chapter:**

> When Lost Silver was refusing to let Trenderman take his measurements for new clothes Trenderman found another way to get him to cooperate after all he can manage to work around all the squirming and moaning.

It was a nice day at the slender mansion where Trenderman had arrived to get the measurements of the pastas to make them clothes. Trenderman got all the measurements he needed except for Lost Silver as he traveled up the stairs to the limbless males room.

"Lost Silver I need to get your measurements so I can make some new clothes" Trenderman says opening the door to the male's room walking in. He saw Silver laying on his bed relaxing as the unknown were floating around.

"I don't need new clothes if you can't tell I have no arms or legs so it doesn't really matter" Silver says softly rolling on his side the unknown floating around him. Trenderman sighs as he walked over and sat on the bed.

"Even without limbs you still need new clothes Silver" He says rubbing Silver's back the smaller male grumbling.

"I don't want new clothes" Silver says sitting up and staring at Trenderman. Trenderman sighs a bit as he rubbed Silver's cheek.

"Yes you do you've had those for far too long" He says softly rubbing Silver's cheek the smaller male slightly leaning into the touch making a soft sound. Upon hearing the soft sound Trenderman was intrigued and rubbed Silver's cheek further.

"Do you like this Silver?" He asks as Silver nods humming lightly. Trenderman continued to rub Silver's cheek moving his other hand to the smaller male's side rubbing carefully. Silver's cheeks started to turn red as he made soft sounds Trenderman smiling and rubbing Silver's side more.

"Does this feel good Silver?" He asks Silver humming and nodding.

"Yes it feels nice please rub my sides more" Silver says softly as Trenderman nods moving his second hand to his other side rubbing carefully and gently. Silver lets out a soft sound blushing as Trenderman chuckles and rubs Silver's hips humming softly.

"You're really liking this aren't you Silver" He says smiling as Silver nods moaning lightly when Trenderman ran his hand between Silver's legs. Silver's back arched his figure shuddering as he moans when Trenderman started rubbing his crotch.

"Ahh Tre-Trender" Silver moans out trying to rub against Trenderman's hand, but was having trouble. Trenderman noticed the male's struggle and carefully wrapped his arm around the smaller one's body helping him. Silver moans out when he rubbed against Trenderman's hand with his help panting softly.

"Ahh Trenderman this feels good" Silver moans out blushing deeply while Trenderman chuckles.

"You're making such cute sounds Silver" Trenderman says smiling his tendrils appearing and carefully wrapping around Silver. Silver blushes further feeling the tendrils wrap gently around his frame while he panted. The tendrils gently rubbed and caressed Silver's body making him shudder and shake in pleasure his back arching.

"Ohh my this feels weird but really good" Silver moans out panting and bucking his hips drooling a bit. Trenderman was soon removing Silver's clothes humming letting his tendrils rub and touch Silver's body while he got his tape measurer. While Silver was moaning and shaking in the tendrils hold Trenderman hums getting the measurements of the boy's body.


	9. MaskyxTeen Hoodie

**Summary for the Chapter:**

> "Slenderman is such a stickler Hoodie's technically an adult so why does it matter?" Is a thought that constantly goes through Masky's head.

MaskyxYoung Hoodie

(In this Masky is set around 20 Toby is set around 18 and Hoodie is set around 17 so yes if you do not like this please leave)

:Masky's POV:

Hoodie's a semi late bloomer that's for sure his lower body hit puberty, but his voice was still so cute and girlish. I was sitting on the edge of his bed being so happy I was able to keep him. Yes I'm 20 and Hoodie is 17 I basically had to beg damn Slenderman to keep him since despite the age difference we are very good friends. It was a year ago when I was 19 and Hoodie was 16 it took a bit, but I'm glad Slendy finally agreed. It was about a year later when Slendy brought Toby home. Yeah he's a good and kinda cute teen, but he couldn't compete with Hoodie. Back to what's at hand I came into Hoodie's room to check on him as I sat on the edge of his bed I admired his cuteness rubbing his cheek. Hoodie opened his mouth and pulled my thumb in sucking on it like he would occasionally when he wiggled around. I like myself, thought this was adorable till he started mumbling my name as he sucked on my thumb with 'more meaning'. This is when things went south Slendy walked in seeing me rubbing Hoodie's crotch it's a mutual thing Hoodie let's me help him all the time with masturbation since he finds it embarrassing.

"Masky leave now" I heard Slendy call as I sighed. I tried pulling my hand away from Hoodie's mouth that was till he started biting my thumb not wanting to let go.

"Ow sir he's biting me why do I have to go I'm doing nothing wrong?" I say frowning as Slendy sighs in annoyance.

"I will NOT tolerate pedophilic actions from my proxy" He says walking over gripping Hoodie's chin in a way that made him open and release my thumb.

"Pedoph-What the hell are you talking about I'm just helping him since he's probably having a lude dream I've done this before!" I say frustrated.

"Leave now Masky" Slenderman said stern as I sigh and look to Hoodie who kept saying my real name over and over one of his legs sticking out from under the blankets as he wore shorts his bulge being noticeable.

"Fine" I say walking out as Slendy sighed bringing one of his tendrils out and stuck it in Hoodie's shorts stroking his fair sized member. Hoodie kept saying My name over and over till he came too…

:3rd person POV:

Slendy sighed as he helped his young sleeping proxy.

"Ah Tim!" Hoodie moaned out his back arching as he came panting heavily still fast asleep as Slendy went to tuck him in.

"Tim cuddle please cuddle cuddle" Hoodie whined cutely in his sleep as Slendy sighed and laid beside the younger one to give him what he wants. Thankfully Hoodie didn't notice the difference as Slendy cuddled his small frame. Time passed as Slendy called everyone into the living room once they were all awake, but Hoodie wasn't there. This confused Masky till Slendy spoke.

"Everyone is to stay out of Hoodie's room poor boy has a fever so he is left to sleep for the day" He says as the others nod their head, but Masky was already upstairs. There was just no way he was going to let his cutie be all alone all day long.

:Masky's POV:

I walked into Hoodie's room and went to him feeling his forehead. The poor thing really was burning up didn't help he had at least six blankets on him. I sighed turning his fan on the highest setting and got under the blankets with him. Immediately the smaller frame of Hoodie was cuddled up to me. I heard him panting and mumbling my name. 'Another lude dream?' I think to myself as I rubbed Hoodie's crotch. I blushed when he made a weird, but very cute sound smiling to myself when I heard him moan my name waking up.

"Tim" Hoodie moaned out wiggling as I hummed and stuck my hand in his shorts and boxers rubbing a finger to his surprisingly slick entrance. I asked Hoodie if he wanted this being happy when he said yes I slipped my finger in. Moving the finger around is what set me off the most his cute sounds! Hoodie's voice being so soft made me go crazy with lust as I carefully pulled my finger out and slipped his shorts and boxers off. Hoodie made very weird and cute sounds as I pushed the tip of my hard member to his entrance groaning softly.

"Ah Tim Tim yes ahh" He moaned out in his cute voice making very weird sounds as I pushed the tip in moving in ever so slowly gaining many sounds from the smaller male.

"Mmm Hoodie you feel so tight don't worry I'll be gentle" I say sweetly being underneath him for this as he panted heavily. I was finally fully in moving around gently Hoodie a moaning mess with making weird and cute sounds. I started thrusting gently Hoodie spiraling into even more of a moaning mess. Neither of us notice Toby walked in to check on us, but was now watching as I was just barely thrusting in Hoodie which was by itself making the smaller go crazy with pleasure. I groaned as it felt amazing guess I was a bit too big since Hoodie only came a few short minutes after being a panting and moaning mess.

"Ah Tim Tim Tim Masky Tim ohhh that that felt amazing Tiimmm" He whined and moaned out as I kept moving not even close to cumming. This kid is just way to cute as he wiggled around on me cumming again after another few minutes. I groaned each time his already tight body tightened around me more. I was able to go a bit faster without Hoodie totally turning to pudding on me with all the weird sounds and movements he kept making as he once again came. How many times has this cutie came now three wow I'm getting close wonder how many more times he will cum. Hoodie kept moaning my name as the blankets moved and fell off from covering Hoodie who was moaning loudly Toby was still watching face deep red now when I finally got to the edge. I groan loudly when I came in Hoodie. His back arched high off me as I filled him and he came a fourth time this was amazing because Hoodie was happy about this he had wanted this. Meaning I am NOT a pedophile. I panted lightly while Hoodie panted heavily as I pulled out my cum leaking from his entrance while he laid on his side on me facing outwards as he cuddled me. He squealed upon seeing toby though as I look to him going deep red.

"Ah Toby how long have you been there?!" I say in a panic.

"Basically the whole time do-don't worry I won't tell" He says as I sigh in relief as Hoodie quickly covered himself being embarrassed. I chuckle softly as Toby left and I brought Hoodie to his private bathroom and cleaned him up getting the cutie new underwear along with his shorts. Once I brought Hoodie back to the bed laying him down and laying beside him I covered us up and he cuddled close.

"Love you Tim" He says smiling happily as I held him close.

"Love you too Hoodie" I say being happy as we both drifted off to sleep me being glad Toby never told Slenderman.


	10. EjxMale Reader

**Summary for the Chapter:**

> Maybe you shouldn't of listened to your friend, but hey at least you aren't dead.  
> (y/n) means your name  
> (yf/n) means your friend's name

:Reader pov:

It was late at night when (your friend's name) convinced me to go on a walk in the forest with him. I really didn't want to go since it was so late, but he wouldn't stop asking till I said I would, it was annoying. I follow him quietly looking around at the trees being a bit bored.

"Hey (y/f/n) seriously why'd we have to take a walk so late at night?" I ask questioningly while my friend looked back at me with a smile.

"Because it's fun (y/n) come on nothing's going to get us" He says casually soon looking forward once more. I mumble to myself quietly and continued to walk, until I felt like I was being watched. I stop in my tracks looking around, but I found nothing following us, us? I look around frantically when I didn't see my friend in front of me anymore.

"(Y/f/n), hey where are you!" I say in panic when there was no response, until I heard a crack. I was soon running back towards my house as fast as I could, my heart was racing.

:Third person pov:

(Y/n) soon stopped in from of his house breathing hard. While searching for the house key his body stiffened, there was something behind him. (Y/n) didn't know what it was, he wanted so desperately to get inside, but he didn't want to move in fear of whatever it was would attack him if he moved. (Y/n) stayed still body slowly trembling when there was footsteps walking towards him. He was now shaking badly as the figure approached him from behind. He soon worked up the courage to speak.

"Who are you?" He asks his voice shaky from fear while the figure leaned close.

"Your a pretty fast runner, when your scared (y/n)" The now presumed person whispers into (y/n)'s ear. (Y/n) shook more when he felt a hand grab his wrist.

"Oh and the name's Eyeless Jack, but people call me Ej" The other male says turning (y/n) around.

: Reader's pov:

I was turned around to face the male my body trembling when I heard the name. My eyes widen when I was met with a blue mask, the same blue mask as the one worn by Eyeless Jack. I was about to yell out in fear, but Ej grabbed me and covered my mouth. I was helpless as Ej grabbed my keys. He unlocked the door and brought me inside, soon pinning me to the couch.

"Please don't hurt me!" I cried out hearing Ej chuckle which scared me further. Ej soon got close smirking under his mask.

"I'm not gonna hurt you (y/n). I just want to have you to myself~" He says with a faint purr. I was confused by his words till I jump in surprise feeling him rub my thigh.

"Wha-what are you doing!?" I say in panic and embarrassment since Ej continued to rub my thigh.

"Like I said before, I want you to myself (y/n)" He says humming lightly. I was now blushing lightly since Ej slowly trailed his hand to my crotch rubbing slowly. I let out a low moan hearing Ej chuckle softly.

"You like it now right, (y/n)?" He asks softly while I shyly nod. He hums lightly and unzipped my pants taking my member out. I moan softly when he started to stroke me. Ej smirks seeing that I was enjoying this and started stroking me faster making me moan more.

"Ahh E-Ej ohh nhh, th-this feels good" I say blushing deeply and already panting softly. I look up at him panting softly while he kept stroking me, occasionally rubbing the tip. This pleasure was slowly driving me crazy since I was soon a moaning mess. Ej smirks and was about to pull my pants and boxers down more than they were, but my phone went off. He growled lightly and stopped stroking me which made me whimper a bit. I watched him grab my phone and look at it since I just got a text from (y/f/n). I soon heard him growl more when he set my phone down though, I guess he didn't like what (y/f/n) texted me.

"Sorry (y/n), but I have to go soon your friend is on his way back here and said he'd be here in about 5 minutes" Ej said softly as I soon nod understanding. He sighed a bit before he continued to stroke my member making me moan again.

"I guess I'll just have to have more fun with you next time then" Ej said smirking under his mask stroking me faster. I moan loudly panting heavily as I was starting to get very close.

"Ahh ohh hnn a-ahhh Ej~" I moan out loudly my back arching and eyes closing as I came on myself breathing hard. I pant heavily while Ej hums cleaning me up and fixing my clothes.

"See you around (y/n)" Ej says before leaving my friend arriving soon after. I fully calmed down before he got here thankfully though.

"(y/n) are you okay I'm sorry for leaving you I kinda got lost" (y/f/n) says being a bit embarrassed.

"Yeah I'm fine" You say softly looking at your friend quietly. You decided not to tell (y/f/n) what happened to you though and for the rest of the night you and (y/f/n) decided to stay inside and watch movies having agreed to not walk in the forest at night again.


	11. MaskyxToby

**Summary for the Chapter:**

> Masky had a bad day and ended up accidentally snapping at Toby so he decides to make it up to the twitching proxy.

Slenderman silently walked through the water carrying his proxy Toby.

"Tha-thank you for carrying me Sl-Slenderman the water is ju-just too deep for me to wa-walk through" He says holding onto the other. Slenderman nods quietly and continued to walk finally reaching the shore a couple minutes later. He set Toby down patting his head before turning to teleport home and get changed. Toby pouts a bit, but continued to walk to the cabin him, Masky, and Hoodie were staying at.

Once Toby arrived at the cabin he quietly entered seeing Hoodie and Masky sitting on the couch together. Like usual Toby felt the need to annoy Masky and went over to the two leaning over the back of the couch.

"Hey Ma-Masky how's it going? He-hey Masky Masky?" Toby whined out poking the masked male. Masky sighs in annoyance growling at Toby.

"Toby leave me alone for once damnit I'm trying to relax!" He shouts making Toby flinch. Masky has never yelled at Toby so the teen was confused and startled. Masky frowns realizing his mistake, but was too late.

"Toby wait I didn't mean to yell!" He said getting up to grab Toby, but the boy had already left the room and was now running down the hall with tears in his eyes. Masky immediately felt bad sighing lightly when he sat down.

Toby ran into his room tears rolling down his cheeks his body shaking. The teen managed to sit on his bed before crying into his hands body trembling. Toby cried for a while before laying on his side curling up in a ball his shaking having calmed. He jumped being startled from hearing a knock at his door though slowly uncurling and giving a response.

"Co-come in" He says softly the door opening and Masky walking in making Toby quickly scoot to the headboard of his bed. Masky sighs lightly closing the door before walking to the bed and sitting on the edge.

"Look Toby I'm sorry I didn't mean to yell really I was just stressed from me and Hoodie's work" Masky says reaching out to Toby not being surprised when his hand was hit away. Masky sat there for a few minutes before taking his mask off looking Toby in the eyes making the smaller calm a bit.

"Really Toby I'm sorry I didn't mean to scare you" He says getting closer to Toby who nods quietly. Toby shook when Masky laid a hand on his cheek now staring into the other's eyes a faint blush coming to his cheeks. He blushed further when Masky let out a soft chuckle gently rubbing his cheek then pulling his mouth guard down. Toby was confused and about to ask why Masky did that, but was stopped when the older male's lips were on his. His eyes widened while Masky moved his lips against Toby's not wasting time to let the other understand what was happening either. Masky pulled Toby close scooting on the bed more moving his lips on Toby's a bit rougher and slipping his tongue past the others soft lips. Toby was very confused and shocked to what was happening being limp in Masky's arms while his mouth was invaded by the other's tongue. Masky liked to be in control and pulled Toby into his lap kissing rougher now smirking when he felt a small bulge poking against his stomach that came from Toby.

The smaller male was completely numb to pain so what was this new feeling he got. Finally being able to move his body again he kissed Masky back making a soft whimper when feeling a surge of something in his crotch rubbing against the other as a result. The action made Masky lightly pull away from the kiss a trail of saliva connecting them a soft chuckle leaving his lips.

"Getting excited from just a kiss now are we Toby?" He asks rubbing his hand on Toby's crotch making the boy shiver and moan hips rocking into Masky's touch in response. Toby had no clue what he was feeling or doing since he had no experience or knowledge about sexual acts either. Masky realizing just how innocent Toby really is made him shiver in anticipation since he was going to have fun now. Toby leaned on Masky letting soft moans escape his lips while his hips kept rocking into the rubbing motion of Masky's hand.

"Uwah ahh Ma-Masky wha-what's going on with my bo-body wh-why does it feel so warm and wh-why does it fe-feel so good" He says moaning more and bucking his hips rubbing against Masky's hand on his own now. Masky smirks already enjoying this and unbuttoned Toby's pants slipping them and the boxers down.

"Because you're feeling pleasure Toby feels really good right?" He asks Toby nodding and moaning out holding onto Masky while being on his knees. Toby started thrusting his hips when Masky wrapped his hand around Toby's member and pumped it a few times.

"Oh my Toby very eager aren't you? Such a good boy" Masky says carefully holding Toby's side helping the other stay up while having his second hand wrapped around Toby's member watching the other needily thrust into the contact. Toby was already quite the moaning mess in Masky's arms squeaking and moaning upon feeling a finger push into his body. Masky was already hard and wanting to push into Toby knowing the teen can't feel pain, but didn't want to be rude by doing that. Masky was shocked to feel Toby being so wet managing to get even harder when Toby started begging for Masky to go in him.

"Ah Ma-Masky ple-please go in already I do-don't want to wait a-any longer!"He moans out Masky now wasting no time pulling his finger out and taking his own member out. Toby moaned softly when Masky pulled him down onto his member. Masky groans a bit when he went in fully holding Toby's thighs.

"Fuck Toby you feel amazing!" Masky groans out soon thrusting upwards into the other. Toby moans loudly and started to bounce on the other panting lightly while doing so. Toby pants bouncing faster and moaning out when Masky started thrusting into him harder and faster.

"Ahh Ma-Masky this fe-feels really good!" He says out panting heavily as he bounced faster. Masky grunts stroking Toby with his thrusts loving how tight Toby was.A little bit passes as Toby started to feel a bit strange though.

"Ah Masky I fe-feel weird" He whines out blushing making Masky chuckle.

"Don't worry Toby it just means you're close" He says making Toby nod in understanding. A few more moments passed till Toby let out a loud moan and came on himself Masky grunting and humming in Toby.

"Fuck that felt amazing" Masky says slowly pulling out and rubbing Toby's thighs smiling. Toby pants heavily blushing and nodding while Masky fixed both his own and his pants. Soon enough Toby felt exhausted and fell asleep next to Masky. Masky smiles and gently covered Toby up before leaving the room and returning to the living room to sit beside Hoodie and let the young proxy sleep.


	12. ZalgoxMasky

**Summary for the Chapter:**

> Masky regrets going outside during the night to smoke a cigarette.

It was a late night like usual as everyone was asleep, but Masky was still awake. He stood outside smoking a cigarette trying his best to relax, but even that would soon be over. He was unaware of the unwanted presence looming around him while he sat on the porch. Starting to feel uneasy he looked around quietly before going back to smoking.

"It's probably nothing" He told himself taking a puff from his cigarette coughing lightly. Masky looked around silently feeling a sudden cold chill and knew something wasn't right. Standing up he looked around more putting his cigarette out since he was pretty much done smoking it.

"Who the hell is here!" He says out loudly into the darkness receiving no response though. Masky huffs walking off the porch quietly looking around further still not seeing or hearing anything out of the ordinary. He soon made his mistake by walking into the woods a bit being slammed into a big tree the wind knocked from his lungs. Taking in a sharp, weak, and shaky breath he looked up at what knocked him back eyes widening. Masky was greeted by a big wide evil smile his blood soon running cold and draining from his face.

"Wha-what are you doing here? Wh-why are you attacking me?" He says being frightened to look at Slenderman's sworn enemy Zalgo. Said demon smirks at Masky chuckling darkly his hold on the now terrified proxy not loosening any.

"Well I'm here because a certain proxy wasn't in bed like he should have been Masky~ And I'm going to do something much worse than attack you" Zalgo says with a twisted smirk on his face watching Masky try to figure out what he meant. The proxy yelped in surprise when he felt a hand run up his side. He soon shook violently now realizing that Zalgo wanted sex.

"Wa-wait Zalgo please no don't do this to me!" Masky says being in a panic hearing the other chuckle once more.

"What scared and upset that you can't be saved this time? I'm still very angry about last time when you got away" Zalgo says with a deep growl squeezing Masky a bit and gaining a light shriek from the other. Masky was now in a panic breathing fast and hard before Zalgo rubs his cheeks trying to calm Masky knowing this would be much easier to dominate Masky if he was calm.

"Hush Masky just breathe I won't hurt you or at least I'll try not to I don't want you freaking out during this for once I actually want you to feel comfortable and safe" Zalgo says making Masky look him in the eyes. Masky listened seeing Zalgo had a sincere look in his eyes and nodded quietly taking a few deep breaths and calmed his body Zalgo smiling a bit. Zalgo was happy Masky was going to be willing for this being glad he didn't have to force and possibly hurt the smaller male. Zalgo hums a bit slowly pulling Masky's pants down rubbing his crotch lightly earning a light gasp from the other. However unknown to Zalgo's knowledge Hoodie had woken up looking for Masky and soon left the mansion calling for his friend. Masky perked up hearing Hoodie and whimpered looking up at Zalgo who was clearly very angry now.

"Damn it! Every single damn time before I can start anything with you one of them have to come looking for you!" He says in anger roughly pulling Masky's pants up and leaving. Masky sat on his knees shaking a bit knowing the next time Zalgo gets ahold of him he won't hold back. Masky sighed and looked at Hoodie quietly once he was in sight.

"Hi Hoodie" He says as Hoodie quickly hugged him being worried. Masky quietly hugs back and walked to the mansion with the other.

"Masky why were you out here you know you shouldn't leave the porch" Hoodie says softly making the other sigh.

"Sorry Hoodie I won't do it again" Masky says while they walked back to their room. He felt Zalgo's presence and he knew the other will fuck him whenever he gets the next chance. Masky just hoped for his well being that no one will interrupt this time though. Masky sighs laying down and covered up Hoodie soon laying down and covering up too the two falling asleep. Masky slept with slight anticipation of his and Zalgo's next encounter really just wanting that damn pesky demon to finally leave him alone.


	13. SlendermanxToby

**Summary for the Chapter:**

> Toby couldn't be punished with the normal ways so Slenderman took a different approach to it.

Toby was a new proxy being at the mansion for about a month now. He unlike Masky and Hoodie as far as he knows is the only one that managed to keep his memories of his past. Toby kept it secret being scared that his memory would be completely wiped if Slenderman ever found out. It was hard at times because he would occasionally have sudden outbursts for no reason, well that's how it was in the others eyes, but to Toby he has getting triggered and angered by his memories. He'd always quickly come up with a reason for his outbursts usually blaming it on his tics or at times on his bipolar disorder he had.

Toby was currently walking through the forest getting some fresh air since he recently looked at a framed picture in the mansion. The picture wasn't really anything important thankfully since Toby had seen an old family photo in when he saw it. After that it was only a matter of seconds before the picture was on the floor the glass completely shattered. Toby had been surprised at his own outburst and made sure to clean up the mess before walking out needing to escape from the confused stares of the others inside. Toby was mumbling and twitching while he walked something he always did. Thankfully Toby had decided to leave his hatchets behind not wanting too risk doing something stupid if he had them in the state of mind he was currently in. Suddenly though Toby started feeling weird like he was going around in circles.

"Everything se-seems like it's go-going around in circles," he says to himself twitching some. Soon enough though he couldn't tell left from right and forwards from backwards. His mind was going in circles and he knew that this must be how people get lost here. It must be how Slenderman traps his victims. The forest acted like a maze with no escape. He could tell this is how people that get lost in this forest go crazy at an alarming rate, crying out for help only to be met with a cruel fate. Toby though wasn't allowed to have the same fate as the others that stumble into the forest. after all he was already marked by Slenderman, he was the creatures proxy with no escape, no freedom in the long run. Soon enough his mind was filling with thoughts of many things. Thoughts he never would have, and thoughts he's had almost everyday. The voices in his head started to scream making the teen hold his head and scream too. It wasn't for help, it wasn't for it stop, it was just a scream that had no meaning. Toby didn't know if this sensation would stop until everything suddenly went silent. Almost instantly after the silence Toby went unconscious falling to the forest floor.

Toby was unconscious with no form of telling how long he was. To make matters worse though when Toby did finally wake up he found that he was blindfolded and tied to a chair. The proxy started to panic not knowing what to do, not knowing where he was, and not knowing how much danger he was in. Toby struggled and tried to get free until he felt something wrap around his leg recognizing it as one of Slenderman's tendrils. He was confused to why Slenderman had tied and blindfolded him but stopped struggling when he felt more tendrils wrapping around his body.

"Sir wh-what are you do-doing? Wh-why did you tie me u-up and blindfold me?" Toby asks out his twitching being a bit worse than before since he was so nervous. He tried not to panic when he felt the tendrils wrap around his arms legs and stomach his body being lifted into the air.

"Tobias I am your master so you are to listen to me and not disobey me, yet you keep doing it. You keep making yourself remember and you keep having these outbursts because of it and I've come to the conclusion that you need to be reminded just where you stand in this situation," Slenderman says calmly feeling his proxy shaking in his tendrils. Slenderman really didn't want to punish Toby, make him submit to him, or manipulate him invading his mind and forcing him to obey. He never liked to do that to his proxies it just never felt right to do, but Toby was leaving him with little choices. Toby was confused to how Slenderman would punish him though since he couldn't feel pain and soon realized what would be happening when he felt the tendrils slowly pulling his pants down. The young male started struggling violently trying to get free but he couldn't escape the tendrils grip.

"I don't want to do this as much as you don't want it Tobias but you must learn and this is the easiest solution," Slenderman said voice still calm while he tendrils finally got Tobys pants off and then his boxers. Slenderman watched the teen twitching and shaking but only continued with the punishment. He had already come to terms that he would need to make Toby unstable so he could regain control over his mind and thoughts and knew that violating the boy would do just that. He understood that Toby probably wouldn't trust him much after this but didn't mind that.

Toby was tearing up shaking violently not understanding why Slenderman would result to touching his proxy to make them break and submit. He had trusted Slenderman, felt protected being under his control, but this ruined all of it. Toby whimpers softly when he felt a tendril wrap around his member gasping lightly when said tendril was starting to stroke him slowly. Slenderman watched his proxy whimper and shudder from the sudden probably pleasurable contact and started moving the tendril faster. Slenderman knew he would have to get Toby in a state of bliss to be able to do what he needed so he soon moved a tendril to Toby's entrance. Toby was moaning out from being stroked faster now being so occupied with that he didn't even realize there was a tendril at his entrance until he gasped in surprise when he felt his body get forcefully pushed into by a slick tendril. He soon moaned out again when the tendril inside him wasted no time before moving in and out of Toby looking for the boys sensitive spot his other tendril still stroking Toby at a fast pace. Toby's mind was being filled with pleasure and lust while lewd moans came out of his mouth currently feeling no shame at this point in time. Slenderman knew Toby was getting close and soon his tendril found Toby's sweet spot roughly thrusting into it each time it moved in and out. Slenderman was liking the results he was receiving with this punishment not saying anything when Toby's back suddenly arched and a white liquid came out of Toby's member the teen having came quite quickly.

Toby though his punishment was over however he was wrong and with his body still sensitive because he just came he started to wiggle around when he felt the tendrils start to move again. The teen cried out in surprise and was soon becoming overwhelmed by the stimulation he was receiving so soon after cumming and Slenderman could sense his proxy becoming distressed which is exactly what he needed.

Toby was crying out for it to stop his body twitching and shaking having not been allowed to calm down first was making his body and mind go crazy. Soon enough everything in his mind turned to static when Slenderman entered his mind. Slenderman was surprised with the chaotic organized mess that was Toby's mind and started looking around before finding his memories. Slenderman was about to remove Toby's memories once more until he noticed big gaps in Toby's memories and guessed that the male had already suppressed quite a few of his own memories. Getting back on track though Slenderman went to remove Toby's memories until he became shocked when they started disappearing on their own Slenderman realizing Toby was subconsciously suppressing them to keep them protected from the risk of being removed. He also soon heard the three voices in Toby's head warning him to stop and to leave Toby's mind but he stayed. It was only until Toby's mind started shutting down and forcing Slenderman out was when he finally left. Slenderman was surprised by the amount of free will Toby had and how he was so determined to not let Slenderman take control and remove his memories going as far as to shut his own mind down to force Slenderman out. Slenderman was clearly impressed with his proxy now and decided to let him keep his memories and continue acting how he was. He soon decided to take Toby back to his room carefully laying him on his bed untying him, taking the blindfold off, and lightly covered him with a blanket. A few hours after that encounter Toby woke up and looked around before remembering what happened and felt relieved that Slenderman was okay with this now. He sighs lightly to himself smiling a little before deciding to go back to sleep.


	14. TobyxInsane Male Reader

**Summary for the Chapter:**

> Instead of being taken in by Slenderman Toby was taken to an insane asylum and after a while he meets someone new.

(Instead of Slenderman taking Toby in he was caught and sent to an insane asylum)

Toby hums to himself twitching lightly while sitting in his asylum room looking around at the white walls before sighing softly. He was bored like always since the doctors didn’t give him anything to do. Toby’s mental state was pretty stable though which made it so he was allowed out of his room during the time where the patients would be in the big common room to relax and socialize. Even though he wasn’t very social it was nice to be out of the white room every once in a while, and as if on cue Toby stood up walking to the door just as a doctor unlocked and opened it. Toby smiles at the doctor before walking out twitching lightly and cracking his neck and knuckles while he walked to the common area.  
Everything was doing fine while Toby relaxed in a chair occasionally twitching not even paying attention to his surroundings which made what came next even more startling. Out of nowhere alarms were set off ringing throughout most of the building jumping Toby to the point he fell out of the chair quickly standing up.  
“Code red code red hostile patient escaped confinement and is heading down hallway 3-A towards common room 2-A any available medical staff corner and sedate hostile patient all other patients stay clear,” the voice shouted over the alarm and everything felt like it was going in slow motion. Toby watched the other patients running back to their cells so they wouldn’t get in the way, but he just couldn’t move. A loud crashing sound draw Toby’s attention towards the hallway that was spoken of during the alarm just as a male figure clothed in one of the white asylum outfits with (h/l) (h/c) hair came running into the room with a big grin having a rolling cart with him. Toby just stood there watching the male skid to a stop and swivel on his heels pushing the rolling cart roughly into the hallway watching it collide with a few doctors. A loud demented laughter erupted from them Toby being in shock and got a glimpse of their cold (e/c) eyes.  
“Stay out of my way,” the male says to Toby before quickly turning it to the hallway to see a few more doctors coming through. The male growls and went to run by Toby who just stood there looking to the doctors.  
“Tobias, grab (y/n) he needs to be confined!” One of the doctors shouted to Toby. Toby listened to the doctor and turned his gaze to (y/n) who growled deeply and swung a fist at Toby’s face. The twitching male took the blow slightly stumbling back while watching (y/n) already turning to run off thinking he knocked Toby out. Instead though Toby leaned forward gripping (y/n)’s wrist steadying himself and yanked the male back. (Y/n) was taken aback at this and spun in Toby’s grip throwing another punch at him, but was shocked when his fist was caught. (Y/n) didn’t have much time to think since Toby moved so fast spinning so his arms weren’t crossed, but now (y/n)’s arms were behind his back. Crying out (y/n) now had his arms twisted behind his back and was pinned to the wall by Toby soon shouting at him.  
“How are you even conscious I put everything I had into that first hit!” (Y/n) shouted watching Toby with his (e/c) eyes. Toby only hummed lightly pushing (y/n) against the wall a bit more so he couldn’t get away before he spoke twitching a bit when he did.  
“I ca-can’t feel pain (y/n) so your pu-punches do nothing,” he simply says with a smirk looking deep into (y/n)’s eyes. He couldn’t help what he suddenly felt, he was intrigued by this new patient who was definitely psychotic, and he couldn’t help but be drawn to him. The doctors quickly run over and had Toby hold (y/n) still and got a syringe with a fluid in it and went to inject it into (y/n)’s neck. However upon seeing the needle (y/n) started panic and struggle to get away from the doctors. He was surprisingly stable and just fine until the doctors had took out a needle having to draw blood from (y/n). That exact moment was when the new patient snapped and escaped because he hates to admit it, but he’s terrified of needles.  
“Please don’t I don’t want this I hate needles!” (Y/n) cried out in fear the doctor stopping their advance and looked to Toby. Toby looks back at the doctor and moved so he was holding (y/n)’s hands with one hand and gently gripped the back of his head with the other lightly pushing it to the wall.  
“I-it’s going to be okay (y/n), I pr-promise you will be, they ju-just want to help you,” Toby whispers into (y/n)’s ear to comfort him. To say the least it made the male currently pinned to the wall calm down a bit his breathing calming, but panic went through his body when Toby tilted the male’s head. Toby understood why (y/n) would have a fear of needles and he would’ve made the doctors stop by now if this wasn’t necessary. Sighing to himself he moved his hand so he was gently caressing (y/n)’s cheek coaxing his head to tilt and kept speaking to him to give him something else to focus on. (Y/n) focused on Toby only whimpering when he felt the needle go into his neck and almost as soon as it went in it came back out. Toby watched (y/n) slightly tense up when the needle was put in then slowly let him go surprised when he suddenly started falling backwards the sedative already taking affect. He was shocked at how fast the sedative worked catching (y/n) so he didn’t fall on the floor and looked at the doctors being impressed with how they improved. Soon enough (y/n) was taken back to the room and Toby went back to his laying down on his bed.  
“That wa-was interesting,” he says to himself with a smile. Toby hums softly thinking about (y/n) he just wouldn’t get him out of his mind and decided that he wanted to see him again.  
The rest of the day went by and soon Toby was getting ready for bed when he heard someone humming so he got up and went to the wall of his room pressing his head against it. Toby heard the soft humming and recognized it as (y/n). He was surprised, but smiles to himself while he listened before it stopped and he assumed that (y/n) went to bed so he did too.  
The next day when all the patients were allowed to go to the common room in the morning Toby looked around for (y/n) before walking to the male’s room looking in through the open door. He saw (y/n) sitting on his bed knees to his chest clearly nervous about leaving his room. Toby smiles finding this cute and walked into the room sitting on the bed beside (y/n) and twitched a bit before speaking.  
“H-hey, (y/n) aren’t you g-going to go to th-the common room?” Toby asks casually looking at the male who suddenly jumped and Toby guessed he didn’t notice him enter.  
“Not really, I don’t want to socialize after yesterday,” (y/n) says softly blushing when Toby rubbed his cheek gently. (Y/n) calmed down and relaxed into Toby’s touch smiling to himself a little before sighing a bit. Toby nods in understanding before getting up and started to leave the room. (Y/n) watched Toby get up and he decided to follow him quickly getting up and going after him. Toby found this cute and left the room with (y/n) smiling a bit.  
“You’re re-really cute you know, and I wo-would love to spend more time w-with you,” he simply says watching (y/n) blush before nodding a little turning his head to the side.  
“That sounds alright I guess,” (y/n) says softly while he walked with Toby actually feeling happy to be close to him. Toby walked with (y/n) as over the next few weeks they kept hanging out together before finally being in a relationship and they both were happy that Toby happened to be in the right place at the right time.


	15. JeffxMale Reader

**Summary for the Chapter:**

> Jeff was heading to town to kill some people but after finding a house on the way there he decided to have a little fun instead.  
> This was supposed to be posted alongside the TobyxInsane Male Reader but I lost inspiration for this one so yeah.

Jeff mumbles while he walked through the forest during the night. It’s been quite a while since he had killed someone so he was heading into the town to make someone his newest victim. Walking on a path he caught sight of a house that was surprisingly hidden away from the rest of the town and it looked like people live there so he decided to check it out. Walking towards the building he was cautious and looked through the windows. When he didn’t see anyone he knew who ever was living here was more than likely asleep. Jeff looked up to the second floor smirking when he saw a light on through a balcony leading into a room and got curious. Carefully he started climbing the house before getting onto the balcony seeing a teen male getting undressed and smirked again. Jeff made sure the teen didn’t see or hear him when he opened the glass door and stepped into the room.  
(Y/n) lightly shivered when he felt a sudden breeze coming into the room from the balcony. He didn’t remember opening it, but he shrugged it off pulling his shirt over his head before turning around to close the balcony doors. Soon after (y/n) turned though his mouth was covered and he got pinned to the ground by Jeff and started struggling. He tried to cry out and kick Jeff off, but he wasn’t strong enough to and finally stopped struggling. Jeff smirked down at (y/n) once he stopped struggling and sat on his waist keeping the teens mouth covered.  
“Why hello there. Shouldn’t you be in bed by now~?” Jeff whispered into (y/n)’s ear being delighted when the smaller male shivered. Jeff hums quietly to himself and stared down at (y/n) before speaking again.  
“Don’t scream, or you’re going to be killed,” he says with a stern voice watching (y/n) nod. Afterwards he removed the smaller male’s shirt feeling his trembling chest and running his hands up (y/n)’s body. Jeff smirks when he felt (y/n) twitch when he rubbed his nipples and pinched them lightly chuckling at the gasp he received in response.  
“You’re pretty cute~ I bet your ass is pretty cute too~,” he says smirking when (y/n) blushed deeply from his words. Jeff hums not wasting much more time and started removing the others pants chuckling softly to himself because of (y/n) was acting so shy.  
“Hey no need to be so shy,” he says rubbing (y/n)’s sides with a big smile when he saw a bulge in the (f/c) boxers. After freeing (y/n)’s member he looked at the nervous male before speaking.  
“Alright, how about for now I just give you a blowjob?” Jeff asks watching (y/n) nod. Jeff nods back a bit before taking the tip into his mouth and started sucking on it before slowly bobbing his head. (Y/n) moaned softly from this before relaxing his body and placed a hand on Jeff’s head lightly gripping the black hair.  
“Ahh that feels really good,” (y/n) says blushing and panting lightly. Jeff hummed in response before bobbing his head faster for the one beneath him. (Y/n) was feeling a lot of pleasure from Jeff sucking him off and only lasted a few minutes before cumming in Jeff’s mouth. Grunting lightly from not being warned Jeff swallowed the other male’s cum and pulled off smirking.  
“Wow you didn’t last long~,” he says before redressing (y/n) and helping him up. Jeff helped the teen into bed before going bak to the balcony and spoke once more.  
“See you around, (y/n)~,” he says with a smirk watching (y/n) blush deeply before he left. Being left alone (y/n) sighs to himself before laying down and soon enough fell asleep.


End file.
